Boc-2,5-Dichloro-D-Phenylalanine is a Boc-protected, non-natural amino acid derivative belonging to the phenylalanine family, featuring a substituted benzyl side chain bearing two chlorine atoms at the 2- and 5-positions. It contains a free carboxyl group and an amino group masked as a tert-butoxycarbonyl (Boc) carbamate, with the D stereochemical configuration indicated in the product name and a hydrophobic, halogenated aromatic side chain that can modulate packing and electronic properties in peptide contexts. This protected amino acid is used as a building block for stepwise peptide synthesis and for structure-activity or binding studies where incorporation of a halogenated phenylalanine analogue provides a defined chemical handle for modifying sterics and aromatic character.
CAT No: CP12205
Boc-2,5-Dichloro-D-Phenylalanine is a D-configured, halogenated phenylalanine building block supplied as a Boc-protected amino acid derivative, featuring two chlorine atoms on the aromatic ring that strongly influence sterics and electronics while retaining the amino acid backbone for downstream peptide assembly. This protected form is commonly selected in synthetic workflows where controlled incorporation of a chiral, non-natural aromatic residue is required, such as in the preparation of halogenated peptide analogs and medicinal chemistry intermediates.
1. Peptide Analog Synthesis
Boc-2,5-Dichloro-D-Phenylalanine is used by peptide chemists to introduce a D-amino acid residue bearing a 2,5-dichloro-substituted phenyl side chain into peptide analogs and peptidomimetic scaffolds. The Boc-protected amino group supports its role as a defined coupling partner in protected-amino-acid strategies, enabling the construction of short to mid-length sequences where aromatic halogenation is used to tune conformational preferences, hydrophobic character, and physicochemical properties of the resulting peptide. Research groups developing structure-property series for receptor-binding motifs, protease-stable analogs, or halogenated SAR libraries frequently rely on this residue to maintain stereochemical control at the alpha-carbon while varying other sequence positions.
2. Medicinal Chemistry Intermediates
Boc-2,5-Dichloro-D-Phenylalanine serves as a practical intermediate for medicinal chemistry programs that require a chiral, halogenated amino acid fragment for incorporation into larger bioactive scaffolds. Synthetic teams preparing peptidomimetic linkers, constrained aromatic side-chain motifs, or halogenated amide/peptide-like structures often choose this building block because the dichloro pattern provides a consistent handle for downstream derivatization and property tuning in SAR campaigns. Its protected amino functionality and D-stereochemistry make it a convenient starting point for assembling analog series where the stereochemical outcome and aromatic substitution pattern must be preserved through late-stage coupling steps.
3. Halogenated SAR Building Blocks
Boc-2,5-Dichloro-D-Phenylalanine is frequently employed in structure-activity relationship (SAR) workflows to systematically vary aromatic substitution and stereochemistry within peptide-like constructs. Chemical biology and medicinal chemistry teams use this residue to generate libraries of analogs that differ in hydrophobicity, aromatic electronics, and steric bulk at the side-chain, while keeping the backbone stereochemistry fixed at the D-configuration. The Boc protection supports controlled sequential assembly of modified sequences, helping researchers produce matched sets of compounds for comparative characterization in binding, stability, and property screening assays performed in vitro.
4. Chiral Fragment Library Development
Boc-2,5-Dichloro-D-Phenylalanine is also used in the development of chiral fragment libraries for downstream conjugation and scaffold diversification, where a defined, halogenated aromatic amino acid unit is required as a modular component. In custom synthesis and process development settings, the combination of D-chirality and aromatic dichloro substitution provides a reproducible stereochemical and substitution "signature" that can be carried through multiple synthetic routes to generate analogs for profiling. This makes the building block particularly useful when teams need consistent fragments across parallel programs, such as producing matched intermediates for peptide-derived materials, linker chemistries, or SAR-focused compound sets.
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